Potassium Carbonate → 2-{5-Benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenoxy}-1-(4-benzyloxy-phenyl)-ethanone

HRID 1891437노트

반응식

HRID 1891437 반응식
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:24])[CH2:22]I)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:25]([O:32][C:33]1[CH:34]=[CH:35][C:36]([CH:40]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[CH:44][CH:43]=2)[OH:41])=[C:37]([OH:39])[CH:38]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[CH2:25]([O:32][C:33]1[CH:34]=[CH:35][C:36]([CH:40]([C:42]2[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[CH:44][CH:43]=2)[OH:41])=[C:37]([CH:38]=1)[O:39][CH2:22][C:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:16][CH:17]=1)=[O:24])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 674984815-Benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenolHCID 866649211-(4-Benzyloxy-phenyl)-2-iodo-ethanone

생성물 1

HCID 674988732-{5-Benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenoxy}-1-(4-benzyloxy-phenyl)-ethanone수율 60%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Potassium carbonate (0.165 g, 1.2 mmol) was added to a solution of 1-(4-benzyloxy-phenyl)-2-iodo-ethanone (P4) (0.352 g, 1 mmol) and 5-benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenol (P3) (0.412 g, 1 mmol) were in 40 mL of dry acetone and the mixture was refluxed for 6 hr. After completion of reaction (TLC), the solvent was evaporated and the residue extracted with EtOAc:water (3×40 mL). The organic layers were combined, dried over sodium sulfate and evaporated. The residue was dissolved in EtOAc and chromatographed over silica using hexanes: EtOAc (4:1) to give (0.381 g, 60%) yellowish solid product T3. 1H NMR (400 MHz, CDCl3) δ, 7.88 (d, 2H , J=8.8 Hz, Ar—H2/6), 7.41-7.29 (m, 17H, 2×Ar—H, 3×C6H5), 7.07(d, 1H, J=8.8 Hz, 8.4 Hz), 7.02(d, 2H, J=8.8 Hz, Ar—H3/5), 6.92(d, 2H, J=8.8 Hz, 2×Ar—H), 6.54(dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H4′), 6.5 (d, 1H, J=2.4 Hz, Ar—H6′), 6.04 (d, 1H, J=5.6 Hz, CH—OH), 5.24(m, 2H2O—CH2), 5.13 (s, 2H, PhCH2), 5.04 (s, 2H, PhCH2), 5.0 (s, 2H, PhCH2).

후처리

  1. temperaturethe mixture was refluxed for 6 hr
  2. customAfter completion of reaction (TLC)
  3. customthe solvent was evaporated
  4. extractionthe residue extracted with EtOAc
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. dissolutionThe residue was dissolved in EtOAc
  8. customchromatographed over silica

출처 및 근거

ORD 기록
ord-137d1ee2da3445149b9ad20f647f0a5e
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507549B2

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